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This study explores the use of Theater of the Oppressed (TO) as a liberatory pedagogical tool in educational leadership preparation. Through participatory workshops embedded in leadership courses, students engaged with a scripted school board scenario reflecting anti-CRT and anti-LGBTQ+ tensions. TO enabled students to rehearse leadership responses, reflect on their positionality, and practice decision-making in a safe, imaginative space. Findings highlight TO’s potential to foster empathy, critical reflection, and transformative praxis among aspiring leaders. By disrupting traditional pedagogies, TO offers a humanizing approach to leadership education that aligns with anti-racist and anti-oppressive goals. This work contributes to reimagining leadership preparation as a space for revolutionary rehearsal and liberatory action.